Potassium Iodide → 3-(4-Fluorophenyl)-1-((1-phenylpiperidin-4-yl)methylamino)hex-5-en-3-ol

HRID 2037458Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].[C:16]1([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][NH2:29])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].[K+].CN(C=O)C>CCOC(C)=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]([OH:8])([CH2:5][CH:6]=[CH2:7])[CH2:3][CH2:2][NH:29][CH2:28][CH:25]2[CH2:24][CH2:23][N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:27][CH2:26]2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol (223 mg, 0.97 mmol), (1-phenylpiperidin-4-yl)methanamine (295 mg, 1.6 equiv.), potassium iodide (178 mg, 1.1 equiv.) and DIEPA (186 μL, 1.1 equiv.) were mixed with DMF (5 mL) and heated at 80° C. for overnight. The mixture was diluted with EtOAc (50 mL), washed by water (2×15 mL), brine (2×10 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 12-g silica gel cartridge eluted with a 0˜20% methanol in CH2Cl2 gradient to afford 3-(4-fluorophenyl)-1-((1-phenylpiperidin-4-yl)methylamino)hex-5-en-3-ol (245 mg. 66%).

Workup

washwashed by water (2×15 mL), brine (2×10 mL)
dry with materialdried over Na2SO4
filtrationAfter filtration and concentration
customthe residue was purified by chromatography on a 12-g silica gel cartridge
washeluted with a 0˜20% methanol in CH2Cl2 gradient

Sources & evidence

ORD record: ord-3de8862198ef44f4afba4632d1b6806c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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